There are a handful of key branding milestones in Cindy’s career as a supermodel: the Pepsi ads, the workout tape and the swimsuit calendar. In this clip, we go on location for her calendar shoot in Cabo San Lucas with Marco Glaviano (photographer), Ronnie Stam (hair), and Carol Shaw (makeup), and get a peek behind the scenes. Cindy is as unaffected as ever. She recounts the dietary restrictions of prepping for a swimsuit shoot and complains good naturedly about the heat. She quips that one of the bottoms is way too tiny and pointedly remarks that a swimsuit that looks cheap in real life can photograph beautifully. Cindy also takes a moment to distinguish the different responsibilities of a shoot that she herself commissions versus a regular paid gig. Half of the calendar's proceeds went to fund leukemia research; today, copies can fetch anywhere from $50-$100 on eBay.

The photographs are pretty T&A-heavy. There are a lot of suggestive poses—“backshots” with thongs that generously feature Cindy’s posterior; seriously small bikinis; a topless denim look; and some see-through mesh one-pieces. Cindy’s hair is flipped in a deep side part and tousled with a little saltwater crunch. It’s funny because by this point in the show you know Cindy’s face well enough that you can watch it transform from her regular, talking, House of Style face to her "model" face.

This is also one of the moments where you recall how major Cindy was. Girl is insanely hardbody. Sure, she's thin but it's her muscle tone in those hiiiiiiiiigh-cut late-’80s-early-’90s bathing suit bottoms that's mind-blowing. You can’t really compare it to the musculature of any working model today. It's Sports Illustrated swimsuit issue-esque but even more... honed.

The reason why this shoot is a big deal is because the calendar is such a savvy business move. It recognizes how fickle the high-fashion industry is by broadening her appeal exponentially. Even amongst supermodels, this is what makes Cindy exceptional: She knows that hanging in the back office of a garage or the wall of a college kid's dorm does not preclude selling the romance of a $30,000 evening gown. It’s not about getting bullied by an d-bag photographer and pushy stylist on the set of a men’s magazine shoot. This is a multiple-page advertisement for Cindy by Cindy. “For this kind of thing, because it’s my project, it’s my calendar… I want to see the Polaroids,” she says. “We don’t shoot until Marco and I have agreed that we both think it looks good.” The images are timeless. Marco explains, “I believe that this type of photography, even though they may seem simple now and pin-up-y or whatever, years from now they’re going to weather and age better than the other pictures we do, which are maybe more artistic.”

Helena is sort of like Claudia Schiffer, in that it feels weird to have ever had to introduce the Danish supermodel to fashion fans. For a lot of us, she rolled into our lives in the black-and-white Herb Ritts music video for Chris Isaak’s multiplatinum “Wicked Game.” In it Helena appears near-naked and writhes around in the sand with a super sprung Isaak. The imagery is bewitching and the chemistry bonkers. “She walked up on the set and our eyes made contact,” remembers Isaak. “It was like there was an open book: Everybody read it and said, 'There is a magnetism between these people.'" The three-day shoot in Hawaii came after Helena modeled in Paris for two years, but before that, the 5’ 10” beauty was huge on the pageant circuit. Helena Christensen was crowned Miss Denmark and went on to represent her country at the 1986 Miss Universe pageant.

In fact, if you break down all the supermodels’ CVs and pedigrees, it’s like they’ve been engineered by a secret society of master eugenicists. Being the hot girl in a major video and being a beauty queen is cool but she's also a master linguist. “A model from South America taught me Spanish,” she says. “When you’re from Denmark, you learn a lot of languages because no one speaks Danish. You learn English, German, French. And then I speak Swedish because I’ve got lots of Swedish friends and it’s quite similar. It’s great to be able to speak languages in this business.” She'd also go on to become a respected photographer, open a store in the West Village (Butik), and be appointed creative director of Nylon magazine. No. Big. Deal.

Helena seems appealing and approachable here. She talks about her love of vintage clothing (her mother owned a vintage clothing store in Denmark) and looks unpolished. Whether it’s a post-beauty queen grunge period or her youth, Helena wears simple clothes, looks a wee bit wan and has mussed hair. She looks unkempt and totally badass.

Fashion is one thing, but for this segment House Of Style interviews Cindy Crawford, Amber Valletta, Shalom Harlow, Naomi Campbell, Kate Moss, Helena Christensen and Niki Taylor on the subject of modeling nothing: in other words, posing nude. Of the models, Niki is the only one who opts out of nudity entirely: “My body’s for my man.” Cindy talks about her decision to do Playboy because it exposes her to a new audience that may not read fashion magazines (but who obviously get Playboy for the articles). Kate talks about the appeal of her Obsession ads, with Calvin Klein chiming in to comment on the sensual nature of perfume and how challenging it can be to sell a feeling. He believes the Obsession ads are compelling not just for the nudity, but for the expression on Kate Moss’s face.

Many of the models agree that your relationship with the photographer — and the resulting level of confidence and comfort — is a huge part of why they’d choose to do nude campaigns or editorial; they appear genuinely confused about the backlash. A nude Allure cover image got the magazine banned in some parts of California, and Helena’s topless campaign for Express Jeans led to some store boycotts. Stephanie Seymour sizes up the experience best when she equates nude photos with getting a tattoo: It’s permanent, and can haunt you forever, so you have to take your time to do it right, make sure you’re protected and ensure that the photos are done in good taste.

DEMOCRATIZING FASHION: KEVIN MANCUSO'S HAIR TIPS

Summer hairstyles by hairstylist Kevin Mancuso in 1994.Photo: MTV

To be a teen in the ’90s is to know what it’s like to have a ridiculous hairstyle (or a series of them). It was the era of tiny hair barrettes, over-complicated pigtails, white-girl dreads and French twists. In this how-to hair segment, we have celebrity stylist Kevin Mancuso (trusted stylist to Natalie Portman and Taylor Swift in Central Park, displaying the bemusing summer up-dos that were all the rage in 1994. One liberally employs brightly-colored pipe cleaners. Another involves tiny Björk-style rave twists piled on the crown of the head with ends hanging down to create a fringe. Then there’s the repeated teasing and spraying that felts sections of hair into loose dreadlocks. Finally, there’s a side-parted, gelled, sleek look, with a wee pompadour for a rock-hard coif.

POP CULTURE AND FASHION: MANON RHÉAUME, THE FIRST LADY OF HOCKEY, MODELS

Professional female hockey player Manon Rhéaume in 1994.Photo: MTV

Applying what the boys of Dirt magazine did in their fashion editorial, here we use clothing to call attention to someone regular House of Style viewers may not be familiar with. Manon Rhéaume was the first lady of hockey. A Quebec native, she started skating at 3, and was the first woman to sign to a professional team in 1992 when she joined the Tampa Bay Lightning. She’s the OG Roller Derby Girl and famously turned down an offer to pose nude in Playboy. She also happens to be beautiful.

Here, Manon models Patricia Field and Antique Boutique on the ice. There are metallic jackets with leggings; tiny denim shorts and shrunken shirts; mini-skirts and pigtails. The infantilizing (or “kinderwhore”) trend that was huge in the ’90s is kinda a buzzkill, since Rhéaume’s strong and talented, and the costume changes are interspersed with interviews with her male teammates, talking about her incredible capability and athleticism. In one portion, Rhéaume’s skating around eating a soft-serve ice cream cone, and it looks sort of porn-y. But then she takes a spill and lands on her ass in the changing room, cracking up riotously over the splat of ice cream on the floor, which makes you fall right back in love with her.

X-Girl is the sister line to the X-Large brand, and to commemorate the launch of the collection designed by Sonic Youth’s Kim Gordon and stylist Daisy von Furth, the crew throw a renegade fashion show on Wooster Street, across from Marc Jacobs’s show, produced by indie darlings Sofia Coppola and then-boyfriend Spike Jonze. It is an unspeakably cool gambit: There’s a white sheet spray painted with the logo strung up in the background, and a milling crowd comprised of the likes of Zoe Cassavetes, Donovan Leitch, Francis Ford Coppola, The Beastie Boys, J. Mascis of Dinosaur Jr., and My So-Called Life Christmas ghost Juliana Hatfield. Once the Marc Jacobs show lets out, Steven Meisel, Anna Sui, Bill Cunningham, Linda Evangelista and Linda’s then-boyfriend actor Kyle MacLachlan join the others. Actress Ione Skye (then married to Adam Horovitz) models, as does downtown “It” girl Chloë Sevigny. The director Mike Mills designed the X-Girl logo, and most of the clothes resemble thrifted sportswear pieces. There are carefully cut T-shirts that are inspired by deadstock football jerseys, tennis shirts, and ringer tees (a.k.a. the “uniform for indie rockers”). The two founding designers and Chloë Sevigny were the fit models, so the clothes run small, but the focus of the abbreviated clothes is not on being conventionally sexy. The A-line silhouette of the mini-skirts and thigh-skimming dresses was intended to be flattering, but Gordon and von Furth’s design philosophy eschewed lycra because it was too clingy. Built by Wendy's Wendy Mullin also worked on several of the first collections. She has a scrapbook on her site that recounts some of those early days, and she reminisces on how Kurt Cobain's death had happened so close to the show that it cast a pall over the excitement in the hours leading up to the event.

It’s interesting to note that a lot of the more mall-ready clothes of the era, from Judy’s to Contempo Casuals, featured a lot of slippery, tight near-100% lycra compositions for their baby dolls. X-Girl was more about architectural construction: The short-sleeved, crew-neck dresses were cut narrow but not tight, in order to graze the body without confining it. It was a nod to the crispness of mod, as was the choice for all the models to wear flats. Von Furth also makes sure to note that their trousers are low-slung and intended for the skater girl who does not have to relegate herself to wearing oversized boy’s pants that are not made for her physique. The stove-pipe leg is carried throughout, but with a low-slung, tighter fit around a waist with a flattering, thick band. Gordon is notably 7 months pregnant with a daughter she says she hopes is a riot grrl.

X-Girl was important because it was cool enough to be exclusive and fetch a hefty, limited-edition price tag, but none of the pieces ran north of $60 — a fact that was important to von Furth, who says that most of her peers buy their clothes at vintage stores. She is an obvious fashion and construction nerd, rattling off the exact years the clothes evoke; her deceptively simple design features contributed significantly to the line’s popularity.

X-Girl stores have closed since the production of this segment, though the label still exists in Japan. A collaboration with Nike Sportswear was only available in Japan; there have also been collaborations with various bag brands. Two years after this show, von Furth is quoted in Vice about her styling work on a recent story in Dirt: “There was this cute kid named Mark Ronson [ed note: !!!!!] and it was about the lost generation of 1978… Alligator shirts and puffy down jackets and Rod Lavers.” Kim Gordon continues to work in fashion as well, and collaborated with Surface to Air in 2012. But this segment in 1994 is a huge moment in terms of the way mainstream fashion is being upstaged by streetwear, and how the power dynamic has shifted from the runway to the cool kids downtown. At one point, Sofia points out, somewhat facetiously, “You too can have a fashion show.” The words are enormously prophetic.

This shouldn’t be taken as an invective against Carolyn Murphy’s character but this interview kinda bums me out. The model is extremely versatile, and both Joe Zee (then associate fashion editor at W) and makeup artist Laura Mercier mention in voiceovers that a large part of her magic is that you can do anything with her. They praise her look for essentially being a blank canvas. Carolyn Murphy is beautiful, and I like her hair and the throwback Prada spring 1996 suiting that she’s wearing here. I even like her print campaign from the season, as I do all of the ads she appeared in for Versace, Gucci, Dolce & Gabbana, Estee Lauder, Tiffany & Co., Calvin Klein and Max Mara over the years.

The issue is that I don't love her. Her face is hard to read. I believe that she was a tomboy as she recounts in our interview, but I don’t believe her older brother gives her swirlies on her visits home. The expectations for what models say in mainstream broadcast interviews are very much established at this point, and even though you feel Todd's warmth there’s nothing in this interview that feels special or revealing. I miss Naomi in zit cream talking about her future husband.

Brothers Royston and Antony Langdon of Spacehog at Smilin' Nylon in New York City in 1996.Photo: MTV

Most of what I know about Spacehog comes from Liv Tyler's five year-marriage to bass player and singer Royston Langdon. That said, this segment is charming. There isn’t too much of a service element, since it’s basically about a bunch of English dudes riffing on clothes they’re obviously not keen on wearing for real, but the camaraderie is entertaining, and we get to look at some great New York stores when W. 8th Street was a whole different story, before NYU set on it like a boa constrictor swallowing an egg. Here we have Antony Langdon, Jonny Cragg, the aforementioned Royston and Richard Steel at a now defunct store called Smiling Nylon and The Eye, an aptly named eyeglasses boutique. It is a romp through “very lurid,” gender-bendy, flammable clothing and bug-eyed sunglasses.

OK, this is not the fashion closet of Ugly Betty’s Mode magazine. Nor is this the well-lit, rack-filled paradise in a fantasy Vogue that pays Carrie Bradshaw $5/word. This is the real-life Vogue closet (before such closet tours were everywhere on the internet and demanded that all your sneakers be color-coordinated in tidy cubbies… ahem, GQ) and the tour is conducted by the lovely Anne Christensen (presently the Executive Fashion Director at Glamour) and Lauren Martinez (who, in a particularly fashiony move would go on to marry a Dupont [of the textile magnate Duponts]). The lighting is suboptimal and there are moments when the room is reminiscent of a grandparent’s attic, but we do get a lovely look at the mixed prints, shrunken sweaters, dyed leathers and retro colors that were huge in spring 1996.

Speaking of grandparents’ attics, many of the clothes harken back to the browns, moss greens and burnt oranges of the polyester housedresses and retro kitchen appliances ubiquitous in previous decades, and it’s interesting to see how the runway shows of the year are celebrating clothes that look thrifted and are mismatched. Spring 1996 fashion in a nutshell? The ouroboros of a Vogue editor wearing a beautiful Prada coat that looks like it came from a charity shop advising us on how to thrift a similar look. Where is Todd Oldham when you need him?

As a huge Madonna fan, I was absolutely blown away by how incredible she looked at the 1995 VMAs, when she rocked up to the stage in a satin turquoise Gucci blouse unbuttoned to reveal a sheer bra, and low-slung black trousers, with her blonde hair pouffed and pinned in a half pony. It was fashion magic. Tom Ford had been hired as the Creative Director for Gucci in 1994, and during his first several seasons, he was a beast who seemed to know exactly what type of sexiness we wanted from the then somewhat fusty Italian fashion brand and leather goods label.

Ford came out of the gate hard, channeling the enthusiasm for retro-chic with slightly belled sleeves on micro-mini dresses; sumptuous fabrics like satin and burnout velvet; and wickedly cut trousers. THe knew that a wrapped leather cord that resembled a bolo would look cool and ease us out of our choker rut and injected real glamour back into the house during a time when everyone else was doing quirk. His ads, styled by Carine Roitfeld and shot by Mario Testino, were impeccable, and between 1995 and 1996, the company’s sales increased by 90%.

This runway footage is a continuation of an aesthetic and attitude that Tom Ford mastered during his tenure at the label.

Model Shalom Harlow walks in the first Fashionably Loud in 1996.Photo: MTV

The marriage of music and fashion culminates in the first “Fashionably Loud” that aired in February, 1996. This clip is regrettably brief because of various licensing issues but we thought we’d at least give you a quick glimpse if for no other reason than to see Brandy Norwood walk a runway. It was an-hour long MTV show and for this inaugural event, Chris Isaak hosted. There were models galore with Cindy, Shalom, Amber,Helena, Kate, Linda, Naomi as well as musician-turned-model Debbie Harry. Milla Jovovich our stunning special correspondent pulled double duty to walk and interview audience members.

The designing lineup was just as stellar with collections from Marc Jacobs, Todd Oldham and Anna Sui. The models walked in time to live performances from Coolio, Filter and Elastica (MAJOR girlcrush on Justine Frischmann [ed note: UM, remember when she dated Brett Anderson and founded Suede and then dated Damon Albarn from Blur and inspired a GRIP of music and then co-wrote Arular with her roomie M.I.A? No? Learn about it. Stat.). Totally going to go off and listen to “Connection” right now. That guitar riff is EVERYTHING.

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